Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 9, Pages 2179-2183Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201805208
Keywords
boranes; diastereoselectivity; Ireland-Claisen; sigmatropic rearrangement; silanes
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Funding
- National Research, Development and Innovation Office [K-116150]
- Servier Research Institute of Medicinal Chemistry
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The reductive Ireland-Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland-Claisen product is formed.
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